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  • Leadership & Strategy

Straight Talk: 20 Questions to Improve Employee Conversations

Michele McGovern
By: Michele McGovern
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About the Author

Michele McGovern writes. A lot. These days, she covers HR, digging deep into company culture, DEI, leadership, management and the everchanging world of work. In the years between getting a BA in journalism from a state school and writing about HR, she wrote about big-city crime for a wire service and small-town life for local newspapers. She’s a mediocre mom, decent wife, wannabe athlete and consummate pursuer of fun - on land, snow and water. Find her on LinkedIn @michele-mcgovern-writer.

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Last Updated: May 23, 2026
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Every good manager knows it’s essential to have genuine, meaningful and productive conversations with employees, right?

But most employees say they don’t get the kind of straight talk that would help them in the workplace. Bosses don’t ask questions that are meaningful.

What Gets in the Way of Straight Talk

Employees want to hear more often how they’re doing and where they’re going — even if the conversation isn’t all positive.

In the Manpower Group study, Talk The Talk: How Ongoing Career Conversations Drive Business Success:

  • 82% of employees felt they would be more engaged if they had more meaningful conversations with their bosses more often
  • 78% said they’d be more likely to share their ideas
  • 76% would more likely look for career growth in their company, and
  • 75% would more likely stay with their company.

But here’s the problem: Many managers let other things get in the way of productive conversations. Why? They:

  • Aren’t trained to have the conversations
  • Aren’t prepared to dig deep
  • Are concerned they can’t meet expectations established in deeper conversations, and
  • Don’t understand the benefits of more straight talk about careers, challenges and concerns.

Quality Conversations Deliver Results

It actually pays to have genuine conversations with employees. Good conversations help you align employee motivations and expectations with your organization’s needs. And, as a manager, you can connect with employees to build engagement and understanding.

When managers have more effective conversations with employees, productivity, engagement and loyalty go up.

The research is clear: When managers show genuine interest in their employees’ lives, careers and success, employees are much better at what they do, and the organization is much more successful.

Dan Rockwell, a leadership coach and author of LeadershipFreak blog, says powerful conversations help managers and employees connect, clarify, move forward and be more accountable.

“Imagine if we made it a goal to help people see accomplishment and success in themselves,” Rockwell says.

20 Questions to Start, End Conversations

You can do that by asking better questions to kick off and wrap up conversations.

10 Effective Lead-In Questions

Here are 10 questions that can help launch great conversations that lead to employee development and better relationships.

Use any of them at the coffee pot, in performance reviews, when you start the day or when you’re following up on work.

  1. What would make this conversation a success for you today?
  2. What’s giving you the most energy these days – and what does that say about you?
  3. What’s been weighing on your mind most these days?
  4. What are you learning?
  5. What crossroads are you at today?
  6. What would you like to get out of this conversation?
  7. How would you like to move the ball forward?
  8. Would you like me to listen, coach or advise you today?
  9. Where do you think you waste energy?
  10. How have you succeeded since our last conversation?

10 Effective Landing Questions

The way you land or wrap up a conversation can solidify its value to employees and the company.

These 10 questions are useful ways to end important conversations.

  1. If I saw you moving forward as a result of our conversation, what would I see you doing differently?
  2. What’s shifting in how you want to approach things now?
  3. Who might join you as you move forward – someone who you’d want to share your goals with?
  4. What would you like me to ask you next time?
  5. What was useful today?
  6. What seems clearer for you today?
  7. What do you plan to do between now and our next conversation – and when and how?
  8. What does success look like as you move forward?
  9. What worked best for you during our conversation?
  10. What do you need me to stop doing?
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